Monoazo dyestuffs



'' naphthol-l-sulionic acid Patented Dec. 12, 1939 UNITED STATES PATEN T OFFICE MONOAZO Richard Fleischhauer,

' Fech Aniline Works, 1110.,

poration of Delaware enheim, Germany, assignor D YE STUFFS Frankfort-on-the-Mainto General New York, N. Y., a cor- No Drawing. Application June 6, 1938, Serial No.

212,123. In G 4 Claims.

The present invention relates to monoazo dyestufis, more particularly to those of the gen: eral formula:

group, with l-acylamino-6-naphthol-4 sulfonic acids of the general formula:

N H-acyl The monoazo dyestulfs thus obtained ldye wool and silk prepared for instance by treating 1-amino-6- with acylating agents according'to known methods. The present new dyestufis may also be prepared by combining the above described diazo compounds with 1-amino-6-naphthol-l-sulfonic acid in an alkaline medium and treating. the

monoazio dyestuff'thus obtained with acylating T agents. 7 In order tofurther illustrate my invention the following examples are given, the parts being by weight.

ermany June 9, 1937 (01. 2so 199) I Example 1 17.3 parts of '1eaminobenzene-2-sulfonic acid are diazotized in the usual manner andthe diazo solution obtained isallowed to run into an aqueous solution of 29 parts of 1-acetyl-amino-6- I naphthol-l-sulfonic acid containing an excess of sodium carbonate. When the combination is complete, the dyestuff formed of the formula:

.is separated and dried. It is a bright-orange red powder, soluble in water and dyeing wool and silk clear orange shades of excellent fastness to light.

The dyestuff exhibits a very good levelling power.

Similar orange dyestuffs which are distiguished by a likewise excellent fastness to light and in some cases by a still increased fastnessto washing and perspiration are obtained by employing as coupling component for the above example 1- methoxy, 7 acetylamino 6 naphthol-l-sulfonic acid, 1 phenoxyacetylamino B-naphthol--sulionic acid, 1-chloracetylamino-G-naphthol-4-sulfonic acid, l-benzenesulfonylamino-6-naphthol- 4-sulfonic acid, 1-carboethoxyamino-G-naphthol- 4-sulfo'nic acid and the like.

Example 2 21.8 parts of 3-nitro-l-aminobenzenee6esulionic acid are diazotized in the usual manner and the diazo solution obtained is combined with an aqueous solution of 29 parts of l-acetylamino- B-naphtholl-sulfonic acid containing an excess of sodium carbonate. The dyestuif formed of the formula:

S OaNa on I I N: g i I I I Q Nao, Nn-co-om is separated and dried. It is an orange-brown powder, soluble in water, dyeing wool from. an acid bath yellowish-orange shadesof good fastnessto' perspiration and very good fastness to light and seawater. levelling power; I

By employing as diazo component for instance l-aminobenzene 2-sulfonic acid, 4 methyl-3- The dyestufi has a good chlor-1-aminobenzene-6-sulfonic acid or 1- acetylamino 3 aminobenzene 4-su1fonic acid, similar dyestufis are obtained which are distinguished by a good levelling power and a very good solubility in water, and which dye wool somewhat more reddish-orange shades of very good fastness to light.

Example 3 25.1 parts of 2-amino-4-methylsulfonylbenzene-l-sulfonic acid are diazotized and the suspension of the diazo compound formed is combined with an aqueous solution of 29 parts of 1- aceytlamino-6-naphthol-4-sulfonic acid containing an excess of sodium carbonate. When the combination is complete, the dyestufi formed of the formula:

BI is separated and dried. It is an orange powder, soluble in water, dyeing wool very yellowish orange shades of very good fastness to light. The dyestuff has a good levelling power.

Example 4 17.3 parts of 1-aminobenzene-2-sulfonic acid are diazotized in the usual manner and the diazo solution obtained is allowed to run into an aqueous solution of 34 parts of l-(p-chloropropionylamino) -6-naphthol-4-sulfonic acid containing an excess of sodium carbonate. When the combination is complete, the dyestuff formed of the formula:

Naol NH-CO-CHzCHz-Cl is separated and dried. It is a reddish-orange powder, soluble in water, dyeing wool from an acid bath clear orange shades of excellent fastness to light and good fastness to washing and perspiration.

By employing as coupling component for the above example the corresponding amount of 1- (fi-chlorobutyrylamino) B-naphthol 4 sulfonic acid a similar dyestuff is obtained which is distinguished by an increased levelling power and yields on wool somewhat more yellowish orange shades.

Example 5 The diazo solution obtained by diazotizing 1'7 .3 parts of 1-aminobenzene-2-sulfonic acid is allowed to run into an aqueous solution of 35 parts of l-benzoylamino-G-naphthol--sulfonic acid containing an excess of sodium carbonate. The dyestufi formed of the formula:

8 OaNa OH Na0aS Nib-COO is separated and dried. It is an orange-red powder, soluble in water, dyeing wool from an acid bath very bright orange shades of very good fastness to light and good fastness to washing and perspiration. The dyestuff has a good levelling power.

I claim:

1. The monoazo dyestuffs of the general formula:

HO aS-aryl-N=N HOzS- NH-acyl wherein aryl means a radicle of the benzene series, the --SO3H group being attached thereto in o-position to the azo group and no halogen atom standing in the other o-position to the azo group, which dyestuffs dye wool and silk clear orange shades of very good fastness to light.

2. The monoazo dyestuff of the formula:

S Oa'Na which dyestufi is an orange-red powder, soluble in water, dyeing wool and silk clear orange shades of excellent fastness to light and of good levelling power.

3. The monoazo dyestufi of the formula:

8 O NB NBOaS NIL-G O-CHr-CHr-Cl which dyestufi is a reddish-orange powder, soluble in water, dyeing wool clear orange shades of excellent fastness to light and good iastness to washing and perspiration.

4. The monoazo dyestuff of the formula:

S OsNa N: moss Nil-COO which dyestufi is an orange-red powder, soluble in water, dyeing wool very bright orange shades of very good fastness to light, good fastness to washing and perspiration and of good levelling power.

RICHARD FLEISCHHAUER. 

